66548-20-7Relevant articles and documents
Photochemical Elimination of Molecular Nitrogen from 3,5,5-Trialkyl-3,5-dihydro-4H-1,2,3-triazol-4-ones. Aziridinones, Iminooxiranes and Products
Quast, Helmut,Meichsner, Georg,Seiferling, Bernhard
, p. 225 - 230 (2007/10/02)
The dihydro-1,2,3-triazolones 6 lose molecular nitrogen on irradiation (λ >/= 300 nm).Aziridinones 7, 1:1 mixtures of ketones 10 and isocyanides 11, and small amounts of isocyanates 12 are formed in inert solvents and at temperatures between -90 and +20 deg C.In dimethylformamide as solvent, however, the oxazolidinone -14 arises almost quantitatively from 6c besides traces of acetone and tert-butyl isocyanide (11c).On irradiation in pure methanol, 6b-d produce the α-methoxyamides -17b-d as major product and less acetone and 11c than in inert solvents.In contrast, the presence of sodium methoxide gives rise to the formation from 6c of significant amounts of the α-aminoester -15 besides -17c as well as acetone and 11c.The photolysis of 6c in dimethylformamide and methanol, respectively, is compared to the reaction of 6c in the dark but under otherwise identical conditions.The results are interpreted in terms of the nitrogen-extrusion leading to the acyclic aziridinone isomers 16 which either cyclize to yield the aziridinones 7 and the unstable iminooxiranes 9 or react with dimethylformamide or methanol.
